Neopentylamine
Chemical compound
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IUPAC name 2,2-dimethylpropan-1-amine | |
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ECHA InfoCard | 100.024.890 |
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InChI
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Properties | |
Chemical formula | C5H13N |
Molar mass | 87.166 g·mol−1 |
Appearance | colorless liquid |
Density | 0.74 g/cm3 |
Melting point | −70 °C (−94 °F; 203 K) |
Boiling point | 80–82 °C (176–180 °F; 353–355 K) |
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Occupational safety and health (OHS/OSH): | |
Main hazards | Irritant, Flammable, Corrosive |
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Danger | |
Hazard statements | H225, H302, H314 |
Precautionary statements | P210, P233, P240, P241, P242, P243, P260, P264, P270, P280, P301+P312, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P330, P363, P370+P378, P403+P235, P405, P501 |
Flash point | -13 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N (what is YN ?) Infobox references |
Chemical compound
Neopentylamine is an organic compound with the molecular formula (CH3)3CCH2NH2. It is a colorless liquid. The molecule is the primary amine derivative of neopentane, (CH3)4C.
Like most alkyl amines, it degrades slowly in air.[1]
Synthesis
Neopentylamine is prepared by the reaction of neopentyl alcohol with ammonia in the presence of a hydrogenation catalyst.[2]
Use
It is a common building block.[3] For example, some experimental drugs incorporate this amine.[4][5]
References
- ^ "Neopentylamine 5813-64-9 | Tokyo Chemical Industry UK Ltd". www.tcichemicals.com. Retrieved 2021-03-01.
- ^ US 4495369, Werner, Friedrich; Blank, Heinz U. & Gramm, Gunther et al., "Process for the preparation of neopentylamine", published 1985-01-22, issued 1981-09-22, assigned to Bayer AG
- ^ "Neopentylamine Safety Data Sheet". Fisher Scientific. Retrieved March 1, 2021.
- ^ Biamonte, Marco A.; Shi, Jiandong; Hong, Kevin; Hurst, David C.; Zhang, Lin; Fan, Junhua; Busch, David J.; Karjian, Patricia L.; Maldonado, Angelica A.; Sensintaffar, John L.; Yang, Yong-Ching; Kamal, Adeela; Lough, Rachel E.; Lundgren, Karen; Burrows, Francis J.; Timony, Gregg A.; Boehm, Marcus F.; Kasibhatla, Srinivas R. (2006). "Orally Active Purine-Based Inhibitors of the Heat Shock Protein 90". Journal of Medicinal Chemistry. 49 (2): 817–828. doi:10.1021/jm0503087. PMID 16420067.
- ^ Fraser, Robert R.; Mansour, Tarek S. (1984). "Acidity measurements with lithiated amines: Steric reduction and electronic enhancement of acidity". The Journal of Organic Chemistry. 49 (18): 3442–3443. doi:10.1021/jo00192a059.